DNA-based asymmetric catalysis.
نویسندگان
چکیده
The unique chiral structure of DNA has been a source of inspiration for the development of a new class of bio-inspired catalysts. The novel concept of DNA-based asymmetric catalysis, which was introduced only five years ago, has been applied successfully in a variety of catalytic enantioselective reactions. In this tutorial review, the ideas behind this novel concept will be introduced, an overview of the catalytic chemistry available to date will be given and the role of DNA in catalysis will be discussed. Finally, an overview of new developments of potential interest for DNA-based asymmetric catalysis will be provided.
منابع مشابه
DNA as a chiral scaffold for asymmetric synthesis.
The application of DNA-based hybrid catalysts for enantioselective synthesis has recently emerged. These catalysts, self-assembled from DNA and a metal complex with a specific ligand through supramolecular or covalent anchoring strategies, have demonstrated high enantioselectivity in a variety of carbon-carbon or carbon-heteroatom bond-forming reactions and have expanded their role in asymmetri...
متن کاملThe influence of G-quadruplex structure on DNA-based asymmetric catalysis using the G-quadruplex-bound cationic porphyrin TMPyP4·Cu.
The DNA G-quadruplex-binding porphyrin TMPyP4·Cu was found to form efficient hybrid catalysts for DNA-based asymmetric catalysis when bound to DNA G-quadruplexes. Nucleobase substitution experiments using human telomere-derived G-quadruplex sequences suggest binding of the porphyrin on the 3'-face.
متن کاملDeciphering DNA-based asymmetric catalysis through intramolecular Friedel-Crafts alkylations.
We describe asymmetric intramolecular Friedel-Crafts alkylations with a DNA-based hybrid catalyst and propose a plausible binding model. This study shows promise for studying relationships between the helical chirality of DNA and enantioselectivity of the chemical reaction.
متن کاملDNA-cellulose: an economical, fully recyclable and highly effective chiral biomaterial for asymmetric catalysis.
The challenge in DNA-based asymmetric catalysis is to perform a reaction in the vicinity of the helix by incorporating a small-molecule catalyst anchored to the DNA in a covalent, dative, or non-covalent yet stable fashion in order to ensure high levels of enantio-discrimination. Here, we report the first generation of a DNA-based catalyst bound to a cellulose matrix. The chiral biomaterial is ...
متن کاملOrganic co-solvents in aqueous DNA-based asymmetric catalysis.
Water-miscible organic co-solvents can be used in DNA-based catalytic asymmetric reactions at appreciable concentration without a negative effect on enantioselectivity. While the rate of the copper(II) Diels-Alder reaction is affected negatively by the presence of organic co-solvents, the copper(II) catalyzed Michael addition and Friedel-Crafts alkylation reaction are significantly faster. Addi...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
- Angewandte Chemie
دوره 44 21 شماره
صفحات -
تاریخ انتشار 2005